Getting Over the Fear of Quitting Your 9-5

Last night on Twitter Spaces, the Wealth Wednesday group (Coach Clint, Stephen Wealthy, Tom the Frugal Gay, and me, Adulting Is Easy) invited Jesse Cramer and Brennan Schlagbaum to join to talk about leaving their 9-5s. We picked this topic to mark Tom’s departure from his job last week.


Brennan, perhaps better known as Budget Dog, became a CPA and worked his way up at one of the Big 4 accounting firms. Eventually, his sights turned from business financials to his family’s own, and his passion for personal finance began. Brennan combined this passion with the consistency and dedication he applied to studying for his CPA exam, and the results speak for themselves. In a relatively short time, he was able to replace his 9-5 income with his income from Budget Dog, which he now pursues full time.


Jesse, perhaps better known as The Best Interest, became a mechanical engineer, with both bachelor’s and graduate degrees in the field. While he wasn’t working on telescopes that would be launched into space, he was educating himself and others through his blog. Over time, he found that helping people with their finances was how he wanted to spend his time. Jesse changed 9-5 careers and now helps people money more than full time, with his job and after hours.


Tom, perhaps better known as The Frugal Gay, started investing in real estate at age 21, and hasn’t stopped in the last 18 years. He also runs a resale business, which has supercharged his ability to invest in real estate over the years. Last week, at age 39, Tom left his 9-5 to make his side hustles his main hustle.


Understandably, given these great stories, our conversation revolved around these 3 speakers. (If you missed all or part of the Space, it is recorded and will be posted in the next few days on the Adulting Is Easy podcast feed.) It was evident very early that many listeners had the same question for the speakers: how did you get over your fear of quitting your 9-5?


According to Brennan, fear isn’t the worst thing. It can actually be motivating. He knows his Budget Dog products are how he is providing for his family, and if he doesn’t continue succeeding, he’ll be back in audit. That would motivate me too, Brennan.


Jesse put it a little more bluntly, saying he isn’t worried about stubbing his toe in his career. He too feels like he could go back into the field of mechanical engineering. You only live once, and you must ask yourself how you want to spend your days.


Tom found his answer through a meditation retreat. It turns out when you’re alone with your thoughts for 16 hours a day for multiple days, you realize what’s important to you and what makes you happy. His 9-5 just wasn’t doing that anymore.


If you’re feeling trepidation over leaving your 9-5, it seems the best path is to:

  • Have an emergency fund

  • Pay off a lot (or even all) of your debt

  • Build your side hustle while you’re still working your 9-5

  • Keep in mind that you can always get a job again

As always, I left this Space feeling energized and motivated. Although I’m still a couple of years away from leaving my 9-5, I know what to do when I get closer. And please, join us every Wednesday at 9:30 eastern on Twitter Spaces.


Photo credit: Adolfo Félix

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